The Wittiest Halloween Jokes, Riddles, and Puns

Searching the Web for the very best Halloween humor has been a fun task—more than I could have imagined. I have to admit, though, that in my explorations I was obliged to wade through hundreds of really bad puns, which (with many a groan) I hastened to eliminate from consideration. But my detailed examination also yielded a great many delights. With surprised gratification I learned, for example, that a vampire's favorite ice cream is veinilla (who would've thought?!) and that a ghost with a broken leg is called a "Hoblin Goblin."

As might be obvious, I take great enjoyment in all sorts of word play and creative punning. I also admire the cleverness of those anonymous individuals who feel free to make up new words simply for fun—as in one jokester who informs us that monsters can tell their future by reading their "horrorscope."

The liberty these modern-day jesters give themselves to celebrate this paradoxically dark, yet most whimsical, of holidays feels weirdly refreshing to me. After all, it is a time when adults can be kids again. In fact, Halloween parties for grown-ups may be just as common as those for children (possibly more so?).

As for the kids? Well, on this particular day they're given—or they take—the license to become (almost literally) the very creatures they previously may have most feared. And they're free to indulge in a joyful silliness that's a lot less susceptible to parental criticism than otherwise might be the case. For this is a time when they can do things that ordinarily would be forbidden—or unthinkable: Like dressing up in outrageous (not to say, morbid) costumes and more or less demanding candy from strangers.

I still remember the year when I opened the door to some solitary ghoul and was (rather aggressively, I thought) greeted with the words "trick or treat!" A trifle annoyed by the coerciveness of his tone (and perhaps for the sake of experiment), I replied "trick!"—and was promptly squirted several times in the face with water from a concealed pistol. Who knew he'd actually come "armed"?! Still, on this special night of "licenses," I realized that this (to me) unruly child was quite within his rights. So I really had no choice but to wipe off my face and reach for the bowl of miniature Hershey bars.

Before presenting you with what I regard as the very best examples of Halloween foolery (or, well, lunacy), let me suggest something about how I chose these particular witticisms. In most instances I had to distinguish between that which seemed (to whatever extent) forced, trite, or cornball, from what in my estimation appeared genuinely fresh, imaginative, or clever. And on many occasions only a thin line appeared to separate the two. Most puns on the margin I rejected, though some did make the cut (though just marginally). "What did the boy ghost say to the girl ghost? ‘You look boo-tiful tonight.'" was relatively easy to cut—just too strained. But "What do birds give out on Halloween night?"—the answer being "tweets"—was, to my mind, cute enough to include (i.e., slightly shy of cutesy). . . . But what would you have decided?

Or how about this one? "Where did the goblin throw the football?" "Over the ghoul line." Not bad, but just a tad too forced for me. But for you? . . . Or, how about this one? "What do you give a skeleton for Valentine's Day?" "Bone-bones in a heart-shaped box." Not exactly great, but good enough for a chuckle, I thought. And you? . . . Anyhow, I'm sure a number of readers will question some of my judgment calls (for I did, too!).

Before presenting my final selections, I'll provide one more example of my attempts to distinguish between the slightly cornball and the decidedly clever. You can decide whether you agree or disagree. Somewhat reluctantly I said no to "What do you call two witches living together?" "Broommates." . . . But I said yes enthusiastically to "What do you call a witch's garage?" "A broom closet." So—are we on the same page here? . . .

Anyhow, here are the finalists. I hope you get as many giggles, if not guffaws, out of them (or—dare I say—"cackles" or "howls") as I did.

. . . So sit down, maybe with some apple cider, and enjoy!

On Halloween, parents send their kids out looking like me. [And, if so, no wonder he never got any respect!] ~ Rodney Dangerfield

Halloween was confusing. All my life my parents said, "Never take candy from strangers." And then they dressed me up and said, "Go beg for it." I didn't know what to do. I'd knock on people's doors and go, "Trick or treat . . . no thank you." ~ Rita Rudner

This Halloween the most popular mask is the Arnold Schwarzenegger mask. And the best part? With a mouth full of candy you will sound just like him. ~ Conan O'Brien

I dressed up as a veterinarian for a Halloween costume party. I had a lab coat. And I got a couple of stuffed animals for patients and put bandages on them. ~ Tracy Chapman

Nothing on Earth so beautiful as the final haul on Halloween night. ~ Steve Almond

A grandmother pretends she doesn't know who you are on Halloween. ~ Erma Bombeck

Demons are a ghoul's best friend. ~ Anon

Being in a band you can wear whatever you want--it's like an excuse for Halloween everyday. ~ Gwen Stefani

Acting is like a Halloween mask that you put on. ~ River Phoenix

Halloween is the one night a year when girls can dress like a total slut and no other girls can say anything about it. ~ Lindsay Lohan

What do you do when 50 zombies surround your house? [really, think about this one very carefully] . . . Hope that it's Halloween (!!!).

Never forget:

If human beings had genuine courage, they'd wear their costumes every day of the year, not just on Halloween. ~ Doug Coupland

. . . and especially,

"Today you can be Anything you imagine." ~ Anon

And maybe, just maybe, that's what this freakish, bizarre holiday is all about: To remind us to be adventurous, bold, daring—and not get trapped in the everyday routine of our "normal" identity.

NOTE 1: If this assemblage of witticisms tickles your, er-, funny bone, please consider forwarding its link to friends and family. (Remember, in this all-too-serious world we need as many laughs as we can get.). Moreover, to explore in greater depth the anxiety-based foundation of this strange holiday, see my complementary post, "Halloween Quotes: What They Say About Our Fears."

NOTE 2: If you enjoyed this seasonal collection, you might wish to look at another—non-seasonal, "PG-rated"—post of mine entitled: "Wittiest Sex Quotes Ever."

NOTE 3: And if you’d like to check out other posts I’ve done for Psychology Today online—on a broad variety of psychological topics—click here.

---To be notified whenever I post something new, I invite readers to join me on Facebook—as well as on Twitter where, additionally, you can follow my frequently unorthodox psychological and philosophical musings.

Cute! I really like your work, Doc - both the serious and the fun stuff. Yesterday I read the "Biological Cock" series, and found your perspective charming. By the way, I apologize if my comments appear multiple times. I'm not trying to nag you; I just seem to have a computer compatibility issue with certain websites.

The joke about the Jack-O-Lantern has the words "diameter" and "circumference" mixed up. Should be: "What do you get when you divide the circumference of a jack-o-lantern by its diameter? Pumpkin Pi." The other way, you get a number smaller than 1 as your answer, and the joke doesn't make sense.

Ah! you've mathematically scrutinized this entry a lot more carefully than I had. Anyhow, I made the change and acknowledge you for catching this. Obviously, the jokester who came up with this knew more from humor than from math.

until I saw the check of $7004, I did not believe that my friends brother could actualie making money in their spare time online.. there sisters neighbour started doing this for under 10 months and just repaid the dept on their house and got a great new Audi Quattro. read what he said http://www.jobs64.com

Since this post is currently on the Top Five Most Popular list, I figured I'd add a riddle to the list. For best effect, it requires both the riddler and the riddlee to know two things: that Wiccans claim that their faith, which includes nature-centric aspects, is descended from faith of witches from centuries ago, and that the punchline is a famous saying (which, in this riddle, becomes a pun). As such, don't expect to hear it from many 7-year-olds: